Of all the art forms, theirs seems to be the toughest. Sure, painters and novelists starve for years in the hopes of getting discovered, and the physical demands of being a dancer are excruciating. But no other craft requires the kind of fortitude and specific skill set that stand-ups need. Combining performing and writing, a stand-up is basically an actor delivering his own material, and unlike being in a band there's no music behind him to fill up the silence. Nope, it's just you, a microphone, and an audience that wants to laugh right now. More than any other art form, you're at your best when it seems like you're not doing anything, just talking.

Because I could never do what comics do, I'm fascinated by their work, which is probably why I find myself drawn to movies about stand-ups. There have been several of late—including Funny People and the documentary Comedian—but what's funny about most of them is that you would never want to break into that business after watching these movies. That's part of why I'm so intrigued by them. I love that world not because it's easy, but because it looks so terribly hard.

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The most recent film about stand-up is the very entertaining Sleepwalk With Me. Based on stand-up Mike Birbiglia's autobiographical one-man show, Sleepwalk With Me stars the comic as the fictional Matt Pandamiglio, who like Birbiglia has a mouthful of a last name and a winningly self-deprecating style. It's a movie about love and commitment and growing up and all that, but it's at its best when it shines a light into the process of becoming a good comic.

On its surface, Sleepwalk With Me isn't a lot different from Private Parts, the film of Howard Stern's life, which showed the radio host discovering his voice by talking honestly about his day-to-day troubles. That turns out to be the trick for Pandamiglio as well, and in this way films about stand-ups are similar to sports movies in which the underdog has to learn to believe in himself to become a champ. But where sports movies simply require a montage of the hero going through a grueling workout regimen in the safe company of close advisers and guitar music, comics have to go on stage night after night and bomb horribly in front of a hostile paying crowd before they start getting a kernel of a good bit that works.

It's a masochistic impulse to believe that somewhere on the other side of such bad, unfunny material is a pot of gold, and while most people would find that insane, I think it's pretty inspiring. You see a little of this in Sleepwalk With Me, but it's even more pronounced in 2002's Comedian, which followed Jerry Seinfeld (fresh off the success of Seinfeld) after he decided to retire all his old stand-up material and start from scratch. He was famous enough to earn the goodwill of audiences initially, but as he flounders through new bits that don't work, all that fame means nothing if he's not being funny. Witnessing Seinfeld straining to get laughs during the early stretches of Comedian is actually more impressive than watching his polished act later in the film. You see how difficult it is to attain an air of effortlessness.

Sacrifice and dedication underpin every story of a successful artist, and in Sleepwalk With Me Birbiglia illustrates that through Pandamiglio's long-term relationship with his girlfriend Abby (Lauren Ambrose), which starts to get in the way of his career. For Pandamiglio to graduate from bartender to full-fledged comic, he uses his stalled love life as fodder, and the better response he gets, the more it drives a wedge between him and Abby. (Pandamiglio's hangups also present themselves in his dreams—as the title suggests, he has serious, occasionally perilous sleepwalking issues—but they tend to be more whimsical than really funny or poignant.) Birbiglia, who co-wrote and co-directed the film, understands that his stand-up career was built on the back of his old girlfriend, and Sleepwalk With Me is painfully frank about the sometimes jerky things Pandamiglio does to Abby along the way. (Before a particularly cruel section of the movie, Pandamiglio, who narrates the film, reminds the audience that we're supposed to be on his side, a perfect illustration of how deeply comics want you to like them, even when they pretend not to care.)

Pandamiglio/Birbiglia's career aspirations are even more ironic considering that, as with most films about stand-ups, Sleepwalk With Me makes it look like incredibly difficult, lonely work. When you see stand-up concert films like Raw or any of the Richard Pryor movies, it's all rather thrilling. But whether it's TV shows like Louie or Seinfeld or a movie such as Sleepwalk With Me, the profession is presented without much glamor. (For all the Seinfeld episodes that opened with Jerry killing in a club, there were also some plot lines about what a grind that life really is.) It's hard to think of a career that's constantly portrayed in such unflattering ways as that of the stand-up. And even if you're successful at your job, your life still sucks: The rich, famous celebrities at the center of Funny People or The King of Comedy are miserable bastards, constantly worrying if they can stay on top or if someone is going to screw them over. (It's just as clear in Comedian, which illustrates Seinfeld's compulsion to kill himself on the road developing new material.) And yet Pandamiglio wants into that world: He's willing to leave his stable relationship and steady job just for the chance to play some club in Walla Walla.

So why do I find this life so fascinating? Well, in part it's because I don't have the courage to do it myself. It's not just the ability to tell a joke—the great stand-ups also construct a persona that's uniquely theirs. But the art of stand-up is more than that. It's about timing, pacing, the ability to create a rapport with a room full of strangers. It's public speaking where you have to get laughs at a pretty steady clip. And not only do you have to be funny, you have to be funny every time—with new material. As Chris Rock pointed out recently, unlike being in a successful band, a great stand-up can't just go on tour and play the same 10 songs for the rest of his life. The audience expects brand new stuff every time, and they get angry if they hear an old bit. No wonder stand-ups are portrayed as miserable, needy human beings: They devote their lives to a creative endeavor where they can't ever rest on their laurels.

Like a lot of people, I wonder just how deeply committed I am to the work I do, just what depths I would go to in order to reach my dreams. That's where my obsession with movies about stand-ups probably comes from. It's a chance to live vicariously through genuine artists and risk-takers. They may be horribly unhappy people, but there's a purity to them that I really respect. In Comedian, Seinfeld tells up-and-coming comic Orny Adams a story about the Glenn Miller Orchestra that illustrates the commitment that goes into being a stand-up. It's not about "making it," he says—it's something else:

In the end, most of us would rather be the beautiful, happy people in that house. But our lives are so much richer for the poor bastards out there trudging through the snow trying to make us laugh.

Grierson & Leitch is a regular column about the movies. Follow us on Twitter, @griersonleitch.